Potassium Hydroxide → N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-(4-hydroxycarbonylphenyl)carboxamide

HRID 1857152Notes

Reaction equation

HRID 1857152 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33]C)=[O:32])=[CH:27][CH:26]=2)=[O:24])=[CH:18][CH:17]=1.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([OH:33])=[O:32])=[CH:29][CH:30]=2)=[O:24])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22132633N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-(4-methoxycarbonylphenyl)carboxamide

Product 1

HCID 22132774N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-(4-hydroxycarbonylphenyl)carboxamideYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-(4-methoxycarbonylphenyl)carboxamide was dissolved in methanol (3 ml), 33% aqueous potassium hydroxide (1.5 ml) was added, and the admixture was stirred at room temperature for 2 hours. The reaction mixture was washed 2 times with ethyl acetate, and the water layer was neutralized with dilute hydrocholoric acid and extracted 2 times with chloroform. The chloroform layer was dried with sodium sulfate, and the solvent was then removed by reduced-pressure distillation to obtain 34 mg of the title compound (yield: 45%).

Workup

  1. washThe reaction mixture was washed 2 times with ethyl acetate
  2. additionwith dilute hydrocholoric acid
  3. extractionextracted 2 times with chloroform
  4. dry with materialThe chloroform layer was dried with sodium sulfate
  5. customthe solvent was then removed by reduced-pressure distillation

Sources & evidence

ORD record
ord-28d1ff67a3cf4de1b82b067646055d06
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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